Are there any examples of two species taxonomically classified in different biological families that have successfully hybridized and produced viable offspring? If not, is there an example of where reproduction occured with non-viable offspring?
To be clear, I mean regular sexual reproduction that could occur in the natural world outside a lab. Even so, I'd be curious to know if it could even occur in a lab without direct genetic manipulation.
For example, grolar bears which are ursid hybrids between different species in the Ursus genus are known to exist. Also ursid hybrids between bear species in different genuses have been produced in captivity (sloth bear Melursus ursinus x Malayan sun bear Ursus malayanus and sloth bear x Asiatic black bear Ursus thibetanus). Would an extra-familial hybridisation be possible? Would this be more likely in the plant kingdom?
This question is inspired by a separate question on the Gardening SE which hints at a general lack of understanding of the genetic similarity required for cross-pollination in plants. It made me wonder whether there are any exceptions to the general assumption that extra-familial hybridisation is impossible.